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Dating: How Far Can I Go To Encourage a Relationship...

I recently heard through mutual friends about a young woman who had met a man recently and pursued him to the point where she had become a nuisance; and as time went on possibly a stalker. I was asked if I thought she might be dangerous. As far as I could reconstruct the situation, this is what happened:

Sybil (I will call her) met this young man (Richard) at a party. He seemed friendly and interested. In fact, they made arrangements to go together to an outdoor concert. Although the date went well, she thought, Richard did not call her again. After a couple of days, she called him. He seemed friendly but did not suggest that they go out together a second time. She found an excuse to call him the following week; but he seemed strangely distant. He said that he would contact her when he was less preoccupied by work; but he did not.

The two of them went in different directions for the holidays. When Sybil returned, she made a point of contacting one of Richard’s friends. She wanted to know why Richard had not called her. When he told her that he did not know, she asked him to ask Richard! At a later time she contrived to go to a bar which she knew Richard frequented. When on one occasion she did find him there, she went over to talk to him despite the fact that he was with another woman. Evidently Richard became uneasy because he left immediately afterwards. A few months later she texted him about another concert, but did not pursue him further when he did not respond.

I don’t think Sybil’s behavior rises to the level of actual stalking. Different psychological pathways lead to stalking behavior. It can be motivated by a number of ideas, including the desire for revenge. However, in the context of dating, it usually grows out of the stalker imagining that the other person has an affection, or still maintains an old affection, for him, or her. Such behavior is not uncommon and rarely becomes dangerous. Sybil did not think Richard had an unexpressed and hidden passion for her. She understood that he was indifferent to her; but she thought that she could change the way he felt by continuing to put herself forward. What Sybil was demonstrating was a fixed determination to enter into a relationship with someone who plainly had no interest in her. She was clinging and demanding. Her behavior was the sort of thing that would make most women wince even reading about it.

Such unrelenting and unrequited interest paints the aggressive individual—either a man or woman—in an unattractive light. It is not flattering to the individual being pursued, because it gives no consideration to what that other person is feeling. It gives the appearance of being desperate.

Having said that, I have to admit that on rare occasions such determination pays off. (See my blog post, “The Benefits of Asking.”) I remember a woman who trapped a married man she was attracted to in a locked office and tackled him, literally. On more than one occasion she got between him and the door of whatever office she found him in and began kissing him. It was hard for me to imagine anyone being seduced by such assaultive behavior; but in time the man somehow became involved with her. He divorced his wife a number of years later and married her. But I think the response of most men to this sort of approach is contempt.

I have run into a few men over the years, and even fewer women, whom I had to dissuade from pursuing someone who was plainly not interested. When they go too far, they make smaller any chance that that other person might someday be interested in them. And, in general, I try to prevent patients from humiliating themselves.

But it is relatively rare for men and women to violate these ordinary rules of propriety. What is much more common is for men and women to hesitate to encourage a person whom they find attractive. They think that romantic relationships are supposed to happen naturally, spontaneously. They think men and women just sort of run into each other and get to know each other, and then in time develop an intimate relationship. These women go out of their way not to present themselves as Sybil did. They wish to seem self-contained, neutral, as it were. But, the fact is, it is not possible for someone to appear friendly and disinterested at the same time. It is not possible to be neutral. Someone who is not explicitly encouraging comes across as discouraging. There are some men—and many more women—who are so afflicted by this urge to seem self-contained and cool that they go for long periods of time alone, wanting to be in a relationship but not wanting anyone to know that that is what they want. Rather than reach out to someone, they settle for being alone.

This problem is more apparent in women than men. Most men understand that they are supposed to reach out to a woman in order for her to respond; and yet they hesitate. They may be reacting to different fears, but certainly one fear is of the possibility of being rejected. But some women think they are not supposed to let on that they like someone. The man is supposed to take the lead. They do not want to be confused with Sybil.

But, it turns out that some men, like women, are unsure of themselves; and they need to be encouraged. No matter how good-looking or desirable they may be, some men need encouragement. Often, when I can finally persuade a woman to approach a man she is attracted to, the man says later on that he had never before realized she had been interested in him. They are together, but could have been together a long time ago. So, how far should a man, or woman, go to encourage a relationship?

Rules

The rules governing how couples meet and approach each other change over time. In Jane Austen’s day, a woman had no alternative but to wait primly at home until some man came to call. The man had to arrange for an introduction. Any other behavior would have been unseemly. That time is past. It is perfectly appropriate now for a woman—and certainly a man—to approach a casual acquaintance, or a neighbor, or a fellow-worker and suggest going out together for coffee or a drink.

“Oh, I couldn’t do that!” I hear from some women, and sometimes from a man. Such a person often feels isolated and forlorn and thinks there must be something wrong with him or her that makes it impossible to find a partner; but it is this hesitancy to indicate an interest in someone that is at fault. I have seen beautiful and very appealing women—and men—who never date because they cannot bring themselves to be assertive at the very beginning of a relationship.

Suggestions for the man:

You do not have to wait until “you get to know her better” before you ask someone out. It is not essential that you know her at all. Strike up a conversation. It is true that a woman may very well be unwilling to speak to a stranger; but she may talk to you, nevertheless—if you look presentable and smile. The worst that will happen is that she will walk away.

I knew a young man who met someone while waiting to enter a busy restaurant. They spoke for a few minutes. Then, the woman was seated. The young man did not have the courage or initiative to ask for her telephone number. He haunted that restaurant for weeks, but never ran into her again.

In order to live successfully, every opportunity should be exploited. Of course, most times that a man becomes interested in a woman he has met her under more conventional circumstances, such as a party or at work. Usually, then, there are a number of chances to arrange to see each other. But you should not wait for the right moment. Do things now.

If you text or call someone who seems vaguely approachable and she, nevertheless, says that she is busy, you should consider contacting her again some days or weeks later—even if she did not suggest another time when you first spoke to her. If she refuses you a second time without making a suggestion to meet at a different time, you should assume she is not interested in you. To pursue the relationship past this point is to go too far.

You should not conclude that there is something wrong with you. Most times, men and women will not find themselves attracted to each other. There will be other times. Luckily there are very many men and very many women.

Suggestions for a woman:

The social rules now are such that a woman should not hesitate—and a self-confidant woman will not hesitate to speak to any man she meets and knows even a little. Even that small initiative will show interest and encourage the man to consider a relationship. Although most women will hesitate to actually suggest a date to a casual acquaintance, it is perfectly appropriate to suggest doing some particular thing together.

“I like the Yankees too. Maybe you would like to go to a game someday.”

“I have been looking forward to that concert. Would you like to go into the city and see if we can get hold of a couple of tickets?”

It is at this very early stage that most women balk. They want the man to show interest in them; but they cannot show interest first—even if showing interest is precisely what will encourage the man to take the next step. You are supposed to indicate that you find that person attractive. Expressing such an interest does not make you seem needy or unappealing. Merely showing an interest is not seeming desperate!

If a man does not call in the few days following a first date, it is appropriate to call him. If he cannot be reached, or does not call back, calling again would be going too far. If the relationship has gone on for some time, there is more leeway to calling again, but the point of calling is to indicate further interest, not to corral the man against his wishes. A general rule is to go out of your way to show an interest early in the relationship and to refrain from calling later on. Your job is to encourage the man, not to persuade him that you are more desirable than he thinks you to be. Certainly, do not argue about getting together again when he no longer wishes to do so. That would certainly be going too far.

Very great analysis on the structure and norms of today's dating culture. After reading this article and thinking back, there are many oppoutunites I missed out on because I was waiting for the "right moment". Like you mentioned the fear of getting rejected plays a big part in having this mind set and it can definitely be hard to beat this fear; atleast in my case. I guess it is important to realize that any moment can be the "right moment" and fear should not hold you back from success. Thank you for the good read!

I think I'm just on the edge of being diagnosable with Avoidant Personality disorder. I do have an Asperger's diagnosis (I'm a woman). I've been interested in a man who seems to have the same avoidant issues. I'm so afraid of saying something plainly (like: Do you have any romantic interest in me at all?), and he seems to be OK with the status quo, which is somewhere between "just friends" and more than that, with no definition of what the relationship really is. We're both divorced and midddle aged and this has been going on for 5 years. Yup, avoidant personality disorder. (sigh) He seems to fill the some of his emotional needs by meeting loads of people and forming loads of relatively shallow friendships. I am introverted and stay home a lot.

I read a lot of relationship articles on this site, and frankly this is one of the very few that actually seemed worth the read.

While I'm still skeptical about the advice for men (I'm a man, and it's my experience that demonstrating interest ALWAYS makes me seem desperate or needy), the advice for women is spot on. There are a lot of women whom I'd find far more attractive if they showed an interest in me, and there are other women who seem far TOO attractive to ever show an interest in me. Unless they make the first move, though, neither type of woman is even on my radar.